Does the Bible say that it is better to have been born after Christ?

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I will take a stab at this question, and say "Yes" the Bible does teach that it is better, but I caution not reading "better" as meaning "more pleasant," as your question included the statement that you would not have "enjoyed" Judaism much. Instead, it is better for some very specific reasons.

When I read your question, my mind instantly went to Hebrews, because the book of Hebrews is saturated with the idea of "better." As a Son, Jesus is in a better position than the angels. Our gospel is better than the sacrificial system. We have a better Sabbath, a better High Priest, and a better sacrifice. It sounds odd to say, but Hebrews six and eight convey the idea that our position in Christ is founded on better promises. I don't fully grasp how the promises of God get "better" but Hebrews tells us that they do. We also know from Hebrews that we have a better hope and a guarantee of a better covenant (7:19-22). Other ideas in Hebrews include a better country, better resurrection, a better mediator, better blood.

So, yes, in seeing the comparison between before and after Christ, Hebrews seems to be the most comprehensive answer to your question, and the answer it gives is a resounding "Yes!" I believe Hebrews is addressing a situation in which Jewish Christians were continuing to participate in temple worship, with all of its rites and ceremonies. They insisted on practicing circumcision, making the sacrificial offerings, and were essentially trying to Judaize their Christian faith. Why pour low octane fuel into your old Yugo when you have a Ferrari sitting here the runs on jet fuel? That's better!

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Matthew 13:17 NKJV

for assuredly, I say to you that many prophets and righteous men desired to see what you see, and did not see it, and to hear what you hear, and did not hear it.

For the end result of Jesus will end all arguments (anger), depression, anxiety (mental disorders), death, and wipe away every tear.

Ephesians 4:31 NKJV - Ending Anger

Let all bitterness, wrath, anger, clamor, and evil speaking be put away from you, with all malice.

John 3:18 NKJV - Ending Depression

He who believes in Him is not condemned; but he who does not believe is condemned already, because he has not believed in the name of the only begotten Son of God.

Matthew 6:25-34 NKJV - Ending Anxiety

“Therefore I say to you, do not worry about your life, what you will eat or what you will drink; nor about your body, what you will put on. Is not life more than food and the body more than clothing? 26 Look at the birds of the air, for they neither sow nor reap nor gather into barns; yet your heavenly Father feeds them. Are you not of more value than they? 27 Which of you by worrying can add one cubit to his stature?

28 “So why do you worry about clothing? Consider the lilies of the field, how they grow: they neither toil nor spin; 29 and yet I say to you that even Solomon in all his glory was not arrayed like one of these. 30 Now if God so clothes the grass of the field, which today is, and tomorrow is thrown into the oven, will He not much more clothe you, O you of little faith?

31 “Therefore do not worry, saying, ‘What shall we eat?’ or ‘What shall we drink?’ or ‘What shall we wear?’ 32 For after all these things the Gentiles seek. For your heavenly Father knows that you need all these things. 33 But seek first the kingdom of God and His righteousness, and all these things shall be added to you. 34 Therefore do not worry about tomorrow, for tomorrow will worry about its own things. Sufficient for the day is its own trouble.

Revelation 21:4 NKJV - Ending Death and Crying

And God will wipe away every tear from their eyes; there shall be no more death, nor sorrow, nor crying. There shall be no more pain, for the former things have passed away.”

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Was it better to have been born after Christ? Perhaps a good starting point would be to determine what was different after Christ’s incarnating. Jesus confirms that the Holy Spirits relationship with man would change after He was established at the right-hand of God the Father:

John 15:26 But when the Comforter is come, whom I will send unto you from the Father, even the Spirit of truth, which proceedeth from the Father, he shall testify of me:

John 16:7 Nevertheless I tell you the truth; It is expedient for you that I go away: for if I go not away, the Comforter will not come unto you; but if I depart, I will send him unto you.

The Spirit of the Father that raised Jesus from the dead now dwells in us:

Romans 8:1-11 There is therefore now no condemnation to them which are in Christ Jesus, who walk not after the flesh, but after the Spirit. For the law of the Spirit of life in Christ Jesus hath made me free from the law of sin and death…But if the Spirit of him that raised up Jesus from the dead dwell in you, he that raised up Christ from the dead shall also quicken your mortal bodies by his Spirit that dwelleth in you.

Salvation of one’s soul was available before the cross; however the salvation of one’s life was not. This may seem contradictory but let me explain. Consider Jesus and Nicodemus:

John 3:5-10 Jesus answered, Verily, verily, I say unto thee, Except a man be born of water and of the Spirit, he cannot enter into the kingdom of God. That which is born of the flesh is flesh; and that which is born of the Spirit is spirit…Nicodemus answered and said unto him, How can these things be? Jesus answered and said unto him, Art thou a master of Israel, and knowest not these things?

Notice that this conversation takes place prior to the finished work on the cross and notice that Jesus is chastising Nicodemus for not knowing that one must be born of the Spirit. Man's soul has always been saved by the grace of God through the window of faith. However, after the cross the Holy Spirit gives birth to the presence of Christ in our heart. In that we may serve Jesus as Lord. Before the fulfillment of the gospel man was not able to serve Jesus as Lord because man was not aware of whom the Lord was. We have the benefit of serving Jesus as Lord not just by the knowledge of the Gospel, but by the presence of the Holy Spirit that testifies of Christ. Here is a verse that depicts our current condition:

Colossians 3:13 Every man's work shall be made manifest: for the day shall declare it, because it shall be revealed by fire; and the fire shall try every man's work of what sort it is. If any man's work abide which he hath built thereupon, he shall receive a reward. If any man's work shall be burned, he shall suffer loss: but he himself shall be saved; yet so as by fire. Know ye not that ye are the temple of God, and that the Spirit of God dwelleth in you?

We Christians are uniquely equipped with the Holy Spirit whom bears out the will of God the Father, which is Jesus Christ. We are those that are truly related to the Son of God. Jesus made this statement about those that are His relatives:

Matthew 12:50 …whosoever shall do the will of my Father which is in heaven, the same is my brother, and sister, and mother.

The doing of the will of the Father requires the presence of the Holy Spirit and only that life made manifest by the Holy Spirit will stand the test of fire.

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Your question seems a bit 'fuzzy' to me, because you ask for a biblical basis for it being 'better', and yet you talk about 'enjoying it', so I'm not sure what kind of 'better' you're getting at.

Anyway, I'm going to take your question at face value, though - given your rep - I can't help thinking that you already know this.

To be honest, offhand I can't think of any explicit references, nor even implicit ones. But it seems to me that the OT hope for any 'afterlife' was at best a hazy kind of 'maybe'. In that sense, the only thing that an OT Jew had to 'look forward to' was death.

So assuming that your hypothetical 'after Christ' self was a Jew (or gentile) who believed that Christ was the Messiah, and that his resurrection 'proved' that there was life beyond death for us too, I expect that your appreciation of the here-and-now would be improved by not having the existential angst about the 'what next?'.

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